


Friendly Benefits

by existential1rony



Category: Chicago PD (TV)
Genre: F/M, Friends With Benefits, Sexual Tension, Slow Burn, Some Humor
Language: English
Status: Completed
Published: 2020-07-04
Updated: 2020-07-04
Packaged: 2021-03-04 21:53:36
Rating: Teen And Up Audiences
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,791
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/25063441
Author URL: https://archiveofourown.org/users/existential1rony/pseuds/existential1rony
Summary: Hailey has one heck of a proposition for Jay, something that may change everything, but might be just what they need. Afterall, partners and friends help each other with everything, right?
Relationships: Jay Halstead & Hailey Upton
Kudos: 34





	Friendly Benefits

It's been three months since Hailey Upton did her brief stint with the FBI in New York. It was only for two weeks, but if reaffirmed the hidden feelings she and her partner, Jay Halstead, have for each other. Both of them hated not being able to look across their desks at the other, or grab a drink together after a rough day, or just talk in person whenever they wanted; even if their phone minutes went sky high calling the other in those two weeks, it just wasn't the same. Once Hailey returned, there was an even more unspoken agreement between them on their feelings that had been simmering for years, but still neither had acted on it at this point. It even came to the dismay of their coworkers; the whole Intelligence team was waiting on bated breath for Hailey and Jay to get together, none more than Vanessa Rojas, Hailey's roommate. Everyone was sure it would happen once the latter returned from New York. They're actually getting mad because everyone is about to lose their bets they put on them, even Hank Voight had gotten in on the action. But if "stubborn" is one of the worst traits Hailey and Jay have, "oblivious" is a close second, at least oblivious to each wanting to make that romantic leap. Still, things were bound to unravel at some point, it was only a matter of time.

It was a hot Friday in early July when Hailey and Jay found themselves hanging at his place after work in the air conditioning. Everyone else had been game to hit the bar since Voight had officially given the team the whole weekend off, but the two of them weren't feeling a group hangout tonight. Jay offered to open his newest bottle of expensive whiskey and they were on his couch within the hour enjoying it, and themselves. The sexual tension between them seemed to tick up even more each day that passed. Hailey found herself thinking about it more since it was only just this winter she nearly confessed her feelings for Jay completely after he got shot. She knew it wasn't the right time because he couldn't seem to let go of his careless behavior that came with his huge heart; what she didn't expect is that her behavior would become just as spiraling soon after. Needless to say, it had been a long few months and the subject never seemed to come up again. There was a moment there when she first got back and Jay took her to Bartoli's where it _almost_ happened. She got some of the glorious deep dish sauce on her cheek and Jay had leaned in to wipe it off with his thumb, the tension boiling, but right before what was leading to a kiss the owner walked over to say hello. They both secretly took it as a wash and didn't bring the moment back up. But Hailey was thinking of it now, maybe it was the heat, or the expensive whiskey, or the fact that Jay sat unusually close to her tonight, or his tipsy carefree laughter as one glass turned into two which turned into three; his smile lighting the room every time he laughed at one of her jokes or stories. She was still too nervous to "just go for it," but she decided to take a tentative approach.

"So since we've been sharing such silly stuff tonight, I have a question…"

Jay turns to look at her a little more seriously, a small smirk gracing his face and a bit of hesitancy on what she's possibly going to ask. "Okay?.." he simply responds.

"And by all means tell me to shutup if it's too much, but when was the last time you were with a woman?"

Jay's eyes go wide and he almost spits out his drink. "WHAT?"

Hailey goofily flinches, just now realizing how it sounds and tries to backtrack. "I just mean, with how busy we are, and it just seems like we spend so much of our free time together, it just feels like it could have been a while. And I was just curious y'know, I know men have needs, and… oookay, I'm going to shutup now…" Jay starts to laugh a little and Hailey feels instantly relieved that she didn't offend him or cross a line too much.

"You're not wrong, it's been a while…" he finally replies, shrugging.

"Oh? How long is a while? Not Camilla right?"

"Geez Hailey, way to bring up a guy's past transgressions!" Jay jokes.

"Sorry, the Greek in me is really coming out tonight, isn't it?" they both laugh at that.

"It was last year… a met a girl in a bar one night, you were hanging out with Adam so I was there solo…" his voice drops and they share a charged look of acknowledgment. "Not normally my thing anymore, but as you said, sometimes a guy has needs."

"Gotcha…" she replies while rubbing off the condensation of her glass, trying to focus on that. "That's still a really long time ago." She practically whispers.

"Gee, thanks. Alright, hot shot, when was your last time? Was it in New York? Here you are judging me." They smile at each other and then she raises her brow suggestively at him and he feels his heart plummet. " _Was it!?_ "

"NO! But seeing your face just now? Totally worth it! You know who my last was…"

"Mhmm." Jay slowly mumbles, for lack of a better response; too gleeful that she hasn't been with anyone recently.

They start to stare at each other again. "Seems like it's been an equally long time for both of us." She manages to murmur out.

"It does, doesn't it?" he asks amused, his heart rate accelerating with each word that passes between them.

"So now that that's confirmed, well I was just thinking since we're friends and all, maybe we can help each other out?"

Jay inches even closer to her on the couch, putting his whiskey down on the coffee table, their thighs pressed against each other now. "What do you suggest? I hope you don't want us to set the other up?" he plays flirtatiously, already knowing that's the furthest thing from her mind.

"Of course not, we've already decided it's been too long, who wants to wait more? We can end our drought right now." She plays right back, her blue eyes twinkling and tugging at Jay's emotions even more.

"I see. Like a 'you scratch my back, I'll scratch yours type of deal?'"

"Yeah, like just some friendly benefits, two partners helping the other out." She put her drink on the table now and goes to continue. "I mean…"

The rest of Hailey's words get cut off as Jay lunges forward and attaches his lips to hers. Once her initial shock wears off Hailey starts to kiss him back in earnest, a strangled moan escaping Jay's mouth… or maybe it was Hailey's. Neither could be too sure as they passionately blended together as one for as long as their oxygen would allow. When they finally break apart it's only for a quick moment while Hailey goes to straddle Jay's lap. Once in this position Jay wastes no time yanking his shirt off while Hailey assists and then he slowly pulls her off as well. His hand dives into her hair, which is now wild, and he pulls down on the back of her neck, dragging their lips together again, their tongues battling for dominance. Hailey slides her hands down Jay's chest and makes her way to his belt, hastily trying to undo it. While she's almost finished with that he's already popped the button open on her jeans and dipping his hands inside from the back pulling her even harder against him. He breaks their kiss again to tease her with clarification.

"So this is just to end our dry spell? Nothing more?" he quirks his eyebrow at her.

"Totally!" she grins at him.

"Copy that!"

And then they're kissing again and things start to speed up at a rapid pace, both fed up with their patience of holding in their yearning for months and years. The pot is boiling and ready to simmer over. After their first round they eventually make their way to the bed where they don't actually go to sleep until hours later. Morning comes too soon, but finds them wrapped in each other's arms. Jay wakes first and he takes a few minutes to just stare at her sleeping beauty in awe. When she starts to stir a little he gives her a soft kiss. She smiles brightly at him and he swears his heart stops.

"So was this just a one time thing?" he asks while smiling back.

"One time? I think we surpassed that by the fourth time." She says flirtatiously shy, her cheeks turn a little red.

He beams back at her. "You know what I mean."

"I do. And I think we can benefit from continually helping each other. It can just be another of our things for now."

"That's good because I think I can use some _help_ in the shower. And later in the kitchen. And maybe tomorrow in my back seat at the beach…"

She wraps her arms around his neck, grins, and kisses him. "Lead the way, Halstead."

* * *

A couple weeks later the gang is hanging at Molly's. Hailey and Jay have been continuing to hook up religiously. Whenever they have a free moment alone, they can't seem to keep their hands off each other. They're still not telling anyone or even addressing what it means to them, just enjoying taking one day at a time. Years of hiding your feelings make it easy to avoid that conversation. Their coworkers had been giving them curious looks all night, but they were too wrapped up in each other to notice. At one point when Hailey saw that everyone was paying attention to Kevin's story of his take down of the day, she reached her hand under the table and slowly slid her hand up Jay's thigh and into his groin. Jay almost choked on his beer, but what a way to go.

"I'm getting kinda tired." Hailey addresses the group a few minutes later while looking at Jay.

"Let me go pee then I'll take you home?" Jay suggests, knowing full well Vanessa drove her there.

"That'd be great, thanks!" she smiles, trying to be as inconspicuous as possible.

Once Jay steps away and Hailey stands so they can eave once he's back, Vanessa eyes her up and whispers to her fishing.

"You've been spending even more time with and at Halstead's recently…"

"Well it's just easier to stay there when I drink instead of worrying about getting back, and it's Summer, we always spend more time together in Summer, doesn't everyone?"

"Uh huh. I see you, Hailey. Don't think I don't. You and Jay have both been way too chipper lately."

Hailey gives her roommate an eye roll right as Jay returns and they both wave to their friends and head out, not allowing time for anymore comments.

Another week goes by and the two of them couldn't be happier with their arrangement. They really are positively giddy and there's no way to hide it, you'd have to be blind to not notice things had changed between the two detectives. The gang was ready for them to come clean and would also like to push them along the way. Almost three and a half years of build up was enough. Little did they know they'd get their chance today, thank the crime Gods for granting them a slow one.

Sometime after lunch Jay addressed Hailey somewhat softly, but loud enough for everyone to hear. "Hey, you want to help me look at the interrogation camera? Apparently it's still recording somewhat grainy."

"Sure, better than re-alphabetizing these old case files." Hailey replies nonchalantly and the two walk out of the bull pen not catching the looks everyone else shares.

When they get down the end of the hall Jay yanks Hailey into observation instead and closes the door, a room no one will be able to see in. He pushes her against the window wall and they instantly start kissing. Before things get too heated Hailey breaks away trying to come to her senses.

" _Jay…_ " she groans as he moves his mouth down her neck. "Should we be doing this here?"

"C'mon, how often do we get a slow day?"

Hailey can't argue with that and the only sound that comes out of her mouth again is moans when Jay starts pulling at her shirt and roaming his hands underneath. She grabs his face and kisses him fiercely as he pushes his lower half into hers and they start grinding against each other. They're actually about to take it to the next level, shocked that they're doing this at the district, but too worked up to care, when they hear a noise in the hall. They quickly break away from each other and try to straighten themselves out. They're almost presentable again when Kim opens the door and steps in with them, a knowing look on her face.

"Sorry, I think I left my coffee mug in here."

"We just wanted to look at how the camera was angled from in here." Jay tells her as Hailey nods along fast and guiltily.

"Of course. Huh, guess my mug isn't in here after all." Kim turns as if she's about to leave, then turns around again. "So, like, can you guys just admit it already to yourselves and us that you're together? Because I took money on the end of this month and everyone thought I was a fool for picking the last date… but I knew you two would still dilly-dally. And I was right that it'd take you this long, but now I'd really like to win before our bets are a complete wash…" Kim casually says to them and starts to walk out before they can respond while they stare at her open-mouthed. She turns around one last time before she's out the door, "Oh, and Hailey, your shirt is still half untucked…" she finishes with a smirk leaving them even more speechless.

They stare at each other in the quiet for a bit, still stunned. "So _that_ just happened!" Jay finally says.

"Yeah, she told us!" Hailey replies and they both chuckle.

"Well then I guess is now a good time to tell you I'm in love with you?" Jay asks with a shy smirk.

"You couldn't tell me at Bartoli's, could you? Would have given us a few extra months and been more romantic than the Observation Room!"

Jay looks speechless again, not catching on to the playfulness in her voice since all of his blood flow is still circulating the lower half of his body instead of his brain. "I—"

Hailey yanks his head back down to hers and silences whatever he was going to say with a passionate kiss. "Shutup, Jay! I love you too!" she whispers when they finally break apart.

"That's good, because I've been meaning to make these _friendly benefits_ more permanent."

He kisses her nose as she tucks in the rest of her shirt, then she grabs his hand to walk out with giddy smiles on their faces. When they round the corner they're met with the rest of their team blocking the hallway and waiting patiently. Kim must have spilled the beans because her, Vanessa, Kevin, Adam, and even Trudy are standing there staring. They can even see Voight looking on from down the hall in the bull pen.

"FINALLY!" Vanessa yells out.

"Aww, look at these two _partners_! Alright, let's give Burgess her money. Can't believe these idiots waited this long. I should have pushed harder!" Trudy exclaims teasingly.

"Love you too, Sarge!" Jay says as him and Hailey sneer and walk past them all, ignoring all the hoots, comments, and stares. After all, they made it clear a long time ago they just needed to follow each other. And in case you're wondering, they never had a dry spell again!

* * *

_[A/N: I have to say I've missed writing the one-shots. I'm glad you guys have enjoyed my multi-chapters, but it's nice to just be one and done sometimes, unlike Hailey & Jay ;) This was just a little light one to pass the time, hope you enjoy it. Next on my agenda may be a prompt list, so we'll see how that goes. Thanks so much for reading and for all of your unwavering support. Stay well & Take care!] _


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